Planned to perfection
Let’s face it. Jon Lester was never coming back to Boston.
The Red Sox will tell you they were outbid. Lester will tell you he felt disrespected with the team’s initial offer in the spring.
But this goes deeper than that. And both sides are to blame.
On July 31, Jon Lester was traded to the Oakland Athletics. At that point in time, it was strictly business. All-Star pitcher, contract year, no agreement on a new deal. You can’t let that player walk away and receive nothing in return.
So the Red Sox sent Lester — along with Jonny Gomes — to the A’s in exchange for slugger Yoenis Cespedes and a draft pick.
On the way out, Lester said all the right things. He thanked Red Sox Nation. He even kept the door open to returning to Boston as a free agent.
From there, theories ran wild: Lester and Red Sox general manager Ben Cherington were in cahoots. The Sox’ ace knew his team needed offense, so he agreed to the trade, all while knowing he’d come crawling back to Fenway on his self-proclaimed hometown discount.
Meanwhile, back here in the real world, the only person Lester had a plan with was his agent. And a brilliant plan it was.
Late Tuesday night, Lester chose to sign with the Chicago Cubs. The deal is worth $155 million over six years, with a $25 million vesting option for a seventh year if he pitches 200 innings in 2020 or 400 innings in 2019 and 2020 combined. It also includes a full no-trade clause, and access to 25 hours of personal flights on a private jet per year.
From a business standpoint, Lester and his agent absolutely crushed it. And, in general, how can you be mad at them for that? You only get one chance to go into free agency at the age of 30 (he’ll turn 31 in January) and be the talk of the town at the Winter Meetings.
The first four days in San Diego this week were known as “The Jon Lester Meetings.” And if you’re Lester, how cool is that? You spend your entire career to get that one opportunity to be stuck in the middle of a bidding war for your services. It’s a position of power that every professional athlete dreams of one day being in.
But it’s only a position you can be in if you choose to test the free agent market.
In the days leading up to last season’s trade deadline, that was indeed Lester’s choice, which was why he finished the year in an Oakland A’s uniform.
I will never knock someone for wanting to test free agency. It’s their right. And Lester, in this case, earned every penny he eventually received from the Cubs.
But while former Sox GM Theo Epstein introduces his new pitcher in Chicago this week, back here in Boston, someone will get the blame for why that press conference isn’t happening at Fenway.
And early indications don’t favor Red Sox brass.
Those strictly pointing the finger at Sox ownership are hung up on Boston’s original offer of $70 million over four years back in March. It was an offer that came just two months after Lester publicly and adamantly declared that he would accept a hometown discount.
During that January meeting with the media at the Boston Baseball Writers’ Association of America awards dinner, Lester even went as far as to point out Dustin Pedroia’s decision to “leave a lot of money on the table” with his latest contract to stay in Boston.
Pedroia signed a seven-year, $100 million extension in July of 2013. It should be noted that the starting-pitching market is much different than the second-base market. Still, the point was made, and Lester’s message was clear.
“I want to be here until they have to rip this jersey off my back,” said the Red Sox ace during that media session in January.
Lester also acknowledged 25-year-old Masahiro Tanaka’s seven-year, $155 million contract with the New York Yankees. So he was well aware of his upcoming market value, at the time.
And while proclaiming his willingness to take a hometown discount, Lester also pointed out the responsibility he had to the Players Union.
“You never want to be the guy that takes the market backwards,” he said.
But once again, Lester seemed to realize that he wasn’t going to get his $155 million over seven years with the Red Sox — which, keep in mind, comes out to $22 million a year.
“I understand, that, to stay here [in Boston], you’re not going to get a free-agent deal,” he said in January. “You’re not going to do it. You can’t. It’s not possible. You’re bidding against one team. I understand that you’re going to take a discount to stay. Do I want to do that? Absolutely.”
Lester followed that up by saying, “But just like [the Red Sox] want it to be fair for them, I want it to be fair for me and my family.”
But what is fair for Lester and his family is market value, something he admitted wouldn’t come from the Red Sox.
What happened next was a spring-training offer of four years at $70 million. Fast forward to December, and it’s that initial offer which reportedly forced Lester to refuse to negotiate until the offseason.
Somewhere in between, business was business, and Lester was traded to Oakland.
Now, the perception is that, at some point early on, business got personal, at least, from Lester’s standpoint.
Most in Boston can’t get over the initial four-year, $70 million offer — which, keep in mind, comes out to $17.5 million a year. Between fans and media, many pointing the finger solely at the Red Sox for not bringing Jon Lester back are caught up in the organization’s “disrespectful” start to what was supposed to be an exclusive contract negotiation.
All the while, I’ve been sitting here since April trying to figure out why Lester and his agent refused to negotiate all season long.
So, just to clarify, one initial offer makes you feel disrespected to the point where you won’t even negotiate?
Ok. Fine. April, May, into mid-June . . . still upset. I get it. You were willing to take a hometown discount, and then you get that offer to start things off. Not what you were looking for. Frustration is completely expected.
But then July rolls along, your team is out of the playoff race, the trade deadline is nearing, your GM once again approaches you about getting to the negotiation table, and you still say no?
“We certainly had a desire to engage on a contract conversation with him and that conversation didn't happen enough for whatever reason,” said Cherington in his post-trade deadline press conference on July 31.
“As we got deeper into the season, [Lester] made it clear that that wasn't something he wanted to focus on right now, and so we honored that desire on his part. And I had a conversation with Jon about how we respected that position, but because of the performance of the team, that meant we both might have to deal with this possibility [of a trade].
“If the team's performance didn't really improve, that meant teams were going to start calling on him and it was something we were going to have to deal with,” added Cherington. “We both knew about that possibility going into this week because we had talked about it. It was a combination of the team's performance and his desire not to focus on his contract right now, which we respect his reasons for.”
At that point, it became clear to me then that Lester wasn’t doing much to live up to his “rip the jersey off my back” comment.
I mean, if you want to be somewhere as bad as Lester expressed he wanted to stay in Boston, wouldn’t you at least get in a room and try to work it out?
One day after Lester signed with the Cubs, Cherington once again discussed his attempts to negotiate with Lester before he had no choice but to trade him.
“I believe there’s no deal that can happen unless you’re able to get in a room and talk about it,” said the Red Sox GM at the Winter Meetings on Wednesday. “You might agree, you might disagree, you might go back and forth. But the only way to actually get to a deal is to be able to get in a room and talk about it. I wish we had been able to do that more.”
And when asked if trading Lester hurt Boston’s chances of re-signing him this offseason, Cherington began his answer by saying, “Remember, we hadn’t been able to have any kind of constructive dialogue about a contract in spring training or during the season.”
Speaking as someone who wanted Lester to remain with the Red Sox long-term, I’ve never been too caught up with the initial offer in spring training.
I never even wanted them to trade Lester, and expressed such, at the time he was dealt. My theory is, if you like a dominant pitcher, don’t trade him. Re-sign him.
But then when I found out that Lester wouldn’t even have the discussion — even when his whole “focusing on the season” excuse made no sense while the Sox were out of the playoff race — I realized that Cherington did what he had to do. He resorted to business. And at that point, if you’re not going to re-sign Lester, then it’s a good business decision to get something for him.
Cherington is right. No contract in the history of professional sports has ever been agreed to if you don’t get in a room and work it out.
It takes two sides to make a deal. And as much as Lester’s side may have felt slighted by the team’s initial offer, he certainly didn’t sound like a guy — in January — who was going to let one bad offer prevent him from discussing the subject at all, even when it came time to rip the jersey off his back at the trade deadline.
When deciphering who to blame in this mess, I just can’t seem to get over the fact that Lester wouldn’t negotiate with the Red Sox until the offseason.
But perhaps that was his plan all along.
In January, Lester admitted to knowing he wouldn’t receive market value from the Red Sox while in exclusive negotiations with them.
Let’s look at what he said again: “I understand, that, to stay here [in Boston], you’re not going to get a free-agent deal. You’re not going to do it. You can’t. It’s not possible. You’re bidding against one team. I understand that you’re going to take a discount to stay. Do I want to do that? Absolutely.”
Of course, saying you’ll take a discount is one thing. Actually going through with it is another.
The only way to avoid that discount was to test free agency in the offseason.
So while some look at Boston’s initial four-year, $70 million offer as a slap in the face, turns out, it was actually the best thing that ever happened to Lester and his agent.
Not only did it lead to a six-year, $155 million deal in the offseason, but it also gave Lester an opportunity to save face in Boston when he refused to take that hometown discount of $135 million over six years — which was the Red Sox’ final offer this offseason.
Now, Lester’s not the bad guy. He shouted “hometown discount,” refused to negotiate on the claims of being disrespected by an initial offer, got caught up in a bidding war that all of baseball was watching, and then signed the second-largest contract for a pitcher in baseball history.
Back here in Boston, most of the blame is being thrown at the Red Sox.
Don’t get me wrong. I wanted them to pony up the money for Lester. This team needs pitching. And I’m much more comfortable with a guy who we know can dominate in this city. Do everything you can to bring “that guy” back, instead of taking a chance with someone who isn’t proven in this market.
For that, I’m not letting the Red Sox off the hook. Not for a second.
They have the money to spend, and they should be more than willing to spend it on someone like Lester. But as we know — and even as Lester pointed out to us back in January — the Red Sox put value on certain players, whether it’s fair within the market or not.
Those pointing the finger solely at the Red Sox will try to convince us that Lester would have accepted a five-year, $110 million deal in the spring — which comes out to $22 million a year — had it been offered instead of an insulting initial offer worth $40 million less than that.
It’s the overwhelming opinion which they’ve turned into a fact: that Lester would’ve signed his $110 million deal and all would have been right in Boston, had it been offered.
What’s that based on, what Lester told people?
If I’m going to believe that, I’d have to believe Lester. And while I’m one of his biggest fans, I can’t ignore the fact that he wouldn’t give the same effort to stay in Boston that he once led us to believe he would, back in January.
You can’t convince me that he was going to accept anything less than market value from the Red Sox in the spring. You just can’t do it. I don’t care what Lester is telling people.
Because walking away and refusing to negotiate for an entire season after one bad initial offer, with a team that was going to have to rip the jersey off his back, makes less sense than the initial offer itself.
It was all part of the plan. And the Red Sox were used as Lester’s biggest bargaining chip. He kept that “love for the city” and “willingness to return” in his back pocket until Epstein went to $155 million and threw in a full no-trade clause to go along with 150 total hours of private flights. All while everyone back in Boston felt bad for the guy who was “disrespected.”
That plan started with a potential hometown discount. It ended with the second-largest pitching contract in the history of the game.
Believe what you want. But Jon Lester was never coming back to Boston.
And both sides are to blame.